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Methyl-2-deoxy-alpha-L-erythro-pentofuranose is a chemically synthesized sugar derivative that belongs to the class of organic compounds known as deoxy sugars. These deoxy sugars are a form of sugar that lack one or more oxygen atoms from the molecule. Methyl-2-deoxy-alpha-L-erythro-pentofuranose is in the L-form, which means it has left-handed stereochemistry, and erythro, indicating that carbon atoms with the same substituents are on the same side. It features a five-membered furanose ring, a structure commonly found in biochemically relevant molecules. The methylation of this derivative may enhance its utility in various biological and medical research processes, although its specific applications can vary widely across different fields.

144301-84-8

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144301-84-8 Usage

Uses

Used in Pharmaceutical Industry:
Methyl-2-deoxy-alpha-L-erythro-pentofuranose is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structural features make it a valuable building block for the development of new drugs, particularly in the context of glycobiology and carbohydrate-based therapeutics.
Used in Biochemical Research:
In the field of biochemical research, Methyl-2-deoxy-alpha-L-erythro-pentofuranose is used as a research tool to study the role of carbohydrates in biological processes. Its presence in the structure of certain biomolecules allows scientists to investigate the interactions between carbohydrates and proteins, as well as their influence on cellular functions.
Used in Diagnostic Applications:
Methyl-2-deoxy-alpha-L-erythro-pentofuranose is used as a diagnostic marker in certain medical tests. Its unique chemical properties can be exploited to detect specific conditions or to monitor the progression of diseases, particularly those involving alterations in carbohydrate metabolism.
Used in Food Industry:
In the food industry, Methyl-2-deoxy-alpha-L-erythro-pentofuranose is used as a flavor enhancer or a sweetener. Its unique taste profile and potential health benefits make it an attractive ingredient for the development of new food products.
Used in Cosmetics Industry:
Methyl-2-deoxy-alpha-L-erythro-pentofuranose is used as an active ingredient in cosmetic products, particularly those targeting skin health. Its potential to modulate cellular processes and promote skin regeneration makes it a valuable component in anti-aging and skin care formulations.

Check Digit Verification of cas no

The CAS Registry Mumber 144301-84-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,4,3,0 and 1 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 144301-84:
(8*1)+(7*4)+(6*4)+(5*3)+(4*0)+(3*1)+(2*8)+(1*4)=98
98 % 10 = 8
So 144301-84-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H12O4/c1-9-6-2-4(8)5(3-7)10-6/h4-8H,2-3H2,1H3/t4-,5+,6-/m1/s1

144301-84-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name Methyl-2-deoxy-α-L-erythro-pentofuranose

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
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More Details:144301-84-8 SDS

144301-84-8Relevant articles and documents

Synthesis and Characterization of π-Stacked Phenothiazine-Labeled Oligodeoxynucleotides

Hashmi, S. A. Nadeem,Hu, Xi,Immoos, Chad E.,Lee, Stephen J.,Grinstaff, Mark W.

, p. 4571 - 4574 (2002)

(Matrix Presented) A facile procedure for the incorporation of N-methyl phenothiazine as the terminal nucleoside in oligodeoxynucleotides is reported. The phenothiazine nucleoside analogue is synthesized and then incorporated into DNA using an automated DNA solid-phase synthesizer. Phenothiazine-labeled oligodeoxynucleotides form stable B-form duplexes with higher melting temperatures compared to unlabeled DNA duplexes.

4'-Thionucleosides via in situ pyranose-furanose rearrangements: A short synthesis of the antiherpes agent 2'-deoxy-5-ethyl-4'-thiouridine via direct coupling of a silylated pyrimidine base with a 4-thiopyranose sugar

Jandu,Selwood

, p. 5170 - 5173 (1995)

Methyl 2-deoxy-3,4-O-thiocarbonyl-β-D-ribopyranoside was converted into the thione carbonate by reaction with thiophosgene. Bromide ion-catalyzed O-S rearrangement produced methyl 2-deoxy-3-O,4-S-carbonyl-4-thio-β-D- ribopyranoside (3a) and the 3-O,4-S isomer 3b. The carbonates were cleaved with ammonia and the 3-O,4-S pyranoside sugar coupled with bis(trimethylsilyl)-5-ethyluracil using trimethylsilyl triflate to provide the antiherpes agenet 2'-deoxy-5-ethyl-4'-thiouridine 9. The reaction proceeded via in situ pyranoside rearrangement of the sugar and subsequent coupling. The pyranoside sugar could also be converted to the furanoside form with Dowes H+ acid resin and coupled in conventional fashion to give the nucleoside. Coupling of methyl 4-O-carbamoyl-2-deoxy-3-thio-β-D- ribopyranoside (4b) with the bis(trimethylsilyl)-5-ethyluracil gave 1-[2-[2- (hydroxymethyl)thiiran-1-yl]-1-methoxyethyl]-5-ethyluracil.

Improved Syntheses of Halofuranose Derivatives with the Desired α-Configuration

Chin, Tsung-Mei,Huang, Liang-Kuen,Kan, Lou-Sing

, p. 413 - 416 (1997)

Chlorination of ribofuranose or 2-deoxyribofuranose derivatives was carried out in a 1,4-dioxane solution of hydrogen chloride. This improved procedure allowed the syntheses of 1-chloro-α-D-ribofuranose and 1-chloro-2-deoxy-α-D-ribofuranose derivatives and offered ease of handling, high yield, and the stereo-controlled α-configuration at C-1.

A nucleobase analogue that pairs strongly with adenine

Minuth, Marco,Richert, Clemens

, p. 10874 - 10877 (2013)

Shaping up for an A: Adenine is the only canonical nucleobase that does not offer a third hydrogen-bonding functionality at its Watson-Crick face, making it difficult to bind with high affinity. A 6-ethynyl-2-pyridone binds more tightly and with greater sequence fidelity than thymine. VdW=van der Waals interactions. Copyright

Regioselective and stereoselective route to N2-β-tetrazolyl unnatural nucleosides via SN2 reaction at the anomeric center of Hoffer's chlorosugar

Bag, Subhendu Sekhar,Talukdar, Sangita,Anjali

, p. 2044 - 2050 (2016)

We are reporting a regioselective and stereoselective route to N2-β-tetrazolyl aromatic donor/acceptor unnatural nucleosides as new class of possible DNA base analogs. The SN2 substitution reaction at the anomeric center of Hoffer's chlorosugar with various 5-substituted aromatic tetrazoles in THF in presence of K2CO3 proceeds with regioselectivity at N2-tetrazoles and stereoselectivity at α-chlorosugar with very good yield. The stereoelectronic and steric effects play a crucial role for the observed outcome which is also supported from a theoretical (DFT) study. The methodology is simple, eco-compatible and the tetrazolyl unnatural nucleosides might find applications in decorating DNA for various biotechnological and DNA based material science applications.

The development of β-selective glycosylation reactions with benzyl substituted 2-deoxy-1,4-dithio-D-erythro-pentofuranosides: enabling practical multi-gram syntheses of 4'-Thio-2'-deoxycytidine (T-dCyd) and 5-aza-4’-thio-2’-deoxycytidine (aza-T-dCyd) to s

Wishka, Donn G.,Lopez, Omar D.,Rudchenko, Vladimir F.,Huang, Guangfei,Bahde, Robert,Kumar, Vineet,Denysenko, Sergiy M.,Zhang, Lianhao,Zhang, Mianji,Teicher, Beverly A.,Morris, Joel

, p. 68 - 95 (2020/10/21)

The lack of effective methods to perform direct β-selective glycosylation reactions with 2-deoxy-1,4-dithio-D-erythro-pentofuranosides has long been a significant stumbling block for the multi-gram synthesis of 4’-thio-2’-deoxy nucleosides. In addition, p

Iron-Catalyzed Radical Cleavage/C?C Bond Formation of Acetal-Derived Alkylsilyl Peroxides

Shiozaki, Yoko,Sakurai, Shunya,Sakamoto, Ryu,Matsumoto, Akira,Maruoka, Keiji

supporting information, p. 573 - 576 (2020/02/20)

A novel radical-based approach for the iron-catalyzed selective cleavage of acetal-derived alkylsilyl peroxides, followed by the formation of a carbon–carbon bond is reported. The reaction proceeds under mild reaction conditions and exhibits a broad substrate scope with respect to the acetal moiety and the carbon electrophile. Mechanistic studies suggest that the present reaction proceeds through a free-radical process involving carbon radicals generated by the homolytic cleavage of a carbon–carbon bond within the acetal moiety. A synthetic application of this method to sugar-derived alkylsilyl peroxides is also described.

2-deoxy-D-ribose derivative

-

Paragraph 0048-0050; 0055-0057, (2020/08/09)

The invention belongs to the field of medicine synthesis, and provides a 2-deoxy-D-ribose derivative (III). When the derivative (III) is used for preparing decitabine, the stereoselectivity is good, and the yield is high. The invention provides a preparation method of the derivative. The preparation method comprises the following steps: step a, carrying out oxygen methylation on 1-position hydroxyl of 2-deoxy-D-ribose; and step b, protecting hydroxyl groups at positions 3 and 5, and further carrying out sulfonation on 1-position oxymethyl. The method is simple and convenient to operate, free of special equipment, good in product purity, high in yield and suitable for industrial production.

Purification method of decitabine intermediate

-

Paragraph 0038; 0039, (2020/07/24)

The invention belongs to the technical field of medicinal chemistry, and particularly relates to a purification method of a decitabine intermediate. The method comprises the following steps: dissolving a decitabine intermediate crude product in a first solvent such as trichloromethane, and adding a second solvent such as methyl tert-butyl ether, so that impurities generated in the synthesis process can be effectively removed, and the proportion of beta-configuration products can be increased when the refined intermediate is subjected to a glycosylation reaction.

Open-Close Strategy toward the Organocatalytic Generation of 2-Deoxyribosyl Oxocarbenium Ions: Pyrrolidine-Salt-Catalyzed Synthesis of 2-Deoxyribofuranosides

Ghosh, Titli,Mukherji, Ananya,Kancharla, Pavan K.

supporting information, p. 7488 - 7498 (2019/11/29)

The reaction of secondary amine salts with 2-deoxy-ribofuranoses under forcible conditions leads to the putative furanosyl oxocarbenium ion that is trapped with various alcohols to provide 2-deoxy-ribofuranosides. The observed anomeric selectivities range from an equimolar mixture to complete α-selectivity in the case of bulky sugar acceptors. Owing to the mechanism and temperature of the transformation, the generated oxocarbenium ion shows little or no facial preference towards the nucleophilic attack of non-carbohydrate acceptors and leads to a mixture of anomers in the case of benzyl and acetyl protected donors. However, the conformationally less flexible tetraisopropylsilyl protected donor reacted with both sugar and non-sugar acceptors in a stereoselective fashion. Besides, the glycosylation with 2-cyanoethanol gave the product with unexpected beta-selectivity presumably due to nitrile effect. The operationally simple organocatalytic protocol provides easy access to otherwise difficult 2-deoxy-ribofuranosides/disaccharides.

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